alexleyenda
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aromatic Organic chemistry problem/ diels alder
Hi,
I had the following exercise to do (the b), I did it logically considering the reagents and formula given, but I have no god damn Idea how the hell
one equivalent of buli would remove both Br and allow the reagent to make a diels-Alder reaction with the reagent in 2). Is anyone able to explain
that / can tell me that i'm wrong and what should happen?
[Edited on 21-10-2015 by alexleyenda]
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Metacelsus
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It looks to be forming a reactive benzyne intermediate.
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CuReUS
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Quote: Originally posted by alexleyenda  | but I have no god damn Idea how the hell one equivalent of buli would remove both Br and allow the reagent to make a diels-Alder reaction with the
reagent in 2). Is anyone able to explain that / can tell me that i'm wrong and what should happen?
|
It is possible,but I don't know how
http://www.orgsyn.org/demo.aspx?prep=v75p0201
https://en.wikipedia.org/wiki/Aryne#.5B4.2B2.5D_cycloadditio...
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UC235
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One equivalent of BuLi will lithiate the arene and generate BuBr as byproduct. Then eliminate LiBr to form the benzyne which is trapped by the diene.
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alexleyenda
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Oh I see, that is really an unusual reaction, thank you UC !
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